Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamides

Matthew Kwok Wai Choi, Wing Yiu Yu, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

97 Citations (Scopus)

Abstract

(Chemical Equation Presented) An operationally simple catalytic system based on [RuCl2(p-cymene)2] was developed for stereoselective cyclization of α-diazoacetamides by intramolecular carbenoid C-H insertion, and β-lactams were produced in excellent yields and >99% cis-stereoselectivity. The Ru-catalyzed reactions can be performed without the need for slow addition of diazo compounds and inert atmosphere. With α-diazoanilides as substrate, the carbenoid insertion was directed selectively to aromatic C-H bond leading to γ-lactam formation (>95% yield).
Original languageEnglish
Pages (from-to)1081-1084
Number of pages4
JournalOrganic Letters
Volume7
Issue number6
DOIs
Publication statusPublished - 17 Mar 2005
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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